185810-88-2

Basic information

• Product Name: (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester
• Synonyms: (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester
• CAS NO: 185810-88-2
• Molecular Weight: 314.454
• Mol File: 185810-88-2.mol

Chemical Properties

• CAS DataBase Reference: (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester(185810-88-2)
• EPA Substance Registry System: (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester(185810-88-2)

Safety Data

• Hazardous Substances Data: 185810-88-2(Hazardous Substances Data)

Upstream product

• 665-27-0 1,5-quinide 
• 185810-84-8 (1S,3R,4R,5R)-3-Benzyloxy-1,4-dimethoxy-6-oxa-bicyclo[3.2.1]octan-7-one 
• 185810-83-7 (1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone 
• 185810-86-0 (1R,4S,5R)-1,4-dimethoxy-6-oxabicyclo[3.2.1]octane-3,7-dione 
• 185810-85-9 (1S,3R,4R,5R)-3-hydroxy-1,4-dimethoxy-6-oxabicyclo[3.2.1]octan-7-one 
• 77-95-2 D-(-)-quinic acid 
• 101906-39-2 Methyl (3R,4R,5R)-3,5-Bis<(tert-butyl)dimethylsilyloxy>-4-hydroxycyclohex-1-ene-1-carboxylate 
• 40983-58-2 methyl shikimate 
• 138-59-0 shikimic acid 
• 950897-46-8 (3R,4S,5R)-3,5-dihydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester 
• 950897-45-7 (3R,4S,5R)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 185810-87-1 (4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester 

Downstream Products

• 185810-89-3 (3S,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-4-methoxy-3-vinyl-cyclohex-1-enecarboxylic acid methyl ester 
• 950897-47-9 (3S,4R,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester 
• 950897-48-0 (3S,4R,5R)-3-[(1RS)-2-bromo-1-ethoxyethoxy]-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester 
• 185810-90-6 (3S,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(2-chloro-acetoxy)-4-methoxy-3-vinyl-cyclohex-1-enecarboxylic acid methyl ester 
• 185810-91-7 (3S,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(2-iodo-acetoxy)-4-methoxy-3-vinyl-cyclohex-1-enecarboxylic acid methyl ester 

Relevant articles and documents

An efficient synthesis of a potential (-)-reserpine intermediate from (-)-shikimic acid of the chiral pool

A highly stereoselective route to the polysubstituted chiral octahydrobenzofuran 12, a potential synthon for the E-ring core in the (-)-reserpine synthesis, is described. The α-bromo acetal 11 was obtained from inexpensive (-)-shikimic acid (3) through a series of highly stereoselective chemical reactions (Scheme). Et3B/Bu 3SnH-Mediated intramolecular radical cyclization of 11 led to compound 12 with the required configuration.

Total synthesis of (-)-reserpine using the chiron approach

A highly stereocontrolled synthesis of ring D/E precursor to reserpine has been developed starting from (-)-quinic acid as a chiral template. The total synthesis of (-)-reserpine is described through the cyclization of an immonium lactam intermediate.